(2S,6S)-2-((tert-butyldimethylsilyloxy)methyl)-6-methyl-piperidine | 1352966-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,6S)-2-((tert-butyldimethylsilyloxy)methyl)-6-methyl-piperidine
• 英文别名: tert-butyl-dimethyl-[[(2S,6S)-6-methylpiperidin-2-yl]methoxy]silane
• CAS: 1352966-42-7
• 化学式: C₁₃H₂₉NOSi
• 分子量: 243.465
• InChiKey: FFXOBJXPFBQNKS-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,6S)-2-((tert-butyldimethylsilyloxy)methyl)-6-methyl-piperidine 在 盐酸 、 barium hydroxide octahydrate 、 pyridine-SO3 complex 、 乙醇 、 20% palladium hydroxide on charcoal 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.75h， 生成 (3R,5S,8aS)-monomorine I
  参考文献：
  名称：

  Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

  摘要：

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.006
• 作为产物：
  描述：

  (S)-benzyl 1-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 17.0h， 生成 (2S,6S)-2-((tert-butyldimethylsilyloxy)methyl)-6-methyl-piperidine
  参考文献：
  名称：

  Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

  摘要：

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.006

文献信息

• 2,6-Disubstituted N-arylsulfonyl piperidines as γ-secretase inhibitors
  作者：Dmitri A. Pissarnitski、Theodros Asberom、Thomas A. Bara、Alex V. Buevich、John W. Clader、William J. Greenlee、Henry S. Guzik、Hubert B. Josien、Wei Li、Michael McEwan、Brian A. McKittrick、Terry L. Nechuta、Eric M. Parker、Lisa Sinning、Elizabeth M. Smith、Lixin Song、Henry A. Vaccaro、Johannes H. Voigt、Lili Zhang、Qi Zhang、Zhiqiang Zhao

  DOI：10.1016/j.bmcl.2006.09.094

  日期：2007.1

  A novel piperidine series of gamma-secretase inhibitors, potentially useful for the treatment of Alzheimer's disease, is disclosed. SAR investigation revealed the requirement for cis-stereochemistry of the substituents attached to the core, which resulted in the chair-like diaxial conformation of the piperidine ring. The series was optimized to provide inhibitors with IC(50)'s in the single-digit nanomolar range. Absolute stereochemistry of the active enantiomer was assigned. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid
  作者：Chada Raji Reddy、Bellamkonda Latha

  DOI：10.1016/j.tetasy.2011.11.006

  日期：2011.11

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.